64396-66-3

Upstream product

• 67-56-1 methanol 
• 21179-27-1 (S)-(+)-N,N,4-trimethylbenzenesulfinamide 
• 64353-47-5 (+)-(S)-N-p-tolylsulfinylpyrrolidine 
• 866993-20-6 (S)-4-methyl-N-(1-phenylethylidene)benzenesulfinamide 
• 672-78-6 methyl p-toluene sulfinate 
• 85565-07-7 N,N-diisopropyl-4-methylbenzenesulfinamide 
• 6873-59-2 N-(4-methylphenylsulfinyl)-N,N-diethylamine 
• 1307296-48-5 (R,S)-N-Benzyl-N-(1-phenylethyl)-p-toluenesulfinamide 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 66558-08-5 4-Methyl-benzenesulfinic acid ((S)-naphthalen-1-yl-phenyl-methyl)-amide 
• 81777-35-7 4-Methyl-benzenesulfinic acid ((R)-2-methyl-1-phenyl-propyl)-amide 
• 20752-48-1 (+)-(S)(C)-(S)(S)-N-(1-Phenylethyl)-p-toluolsulfinamid 

Downstream Products

• 116471-84-2 4-Methyl-benzenesulfinic acid (S)-allyl-methyl-amide 
• 103808-56-6 (+)-octadecyl p-tolyl sulphoxide 
• 111289-39-5 [Isopropyl-((S)-toluene-4-sulfinyl)-amino]-acetic acid tert-butyl ester 
• 116471-85-3 N,N-diallyltoluene-p-sulphinamide 
• 116471-84-2 4-Methyl-benzenesulfinic acid (R)-allyl-methyl-amide 
• 116471-85-3 (R)-N,N-diallyl-p-toluenesulfinamide 
• 6873-54-7 N-phenyltoluene-p-sulphinamide 
• 40723-30-6 (+)-(S)-allyl-p-toluenesulphinamide 
• 6873-86-5 (+)-(S)-isopropyl-p-toluenesulphinamide 

Relevant academic research and scientific papers

Acid catalyzed alcoholysis of sulfinamides: Unusual stereochemistry, kinetics and a question of mechanism involving sulfurane intermediates and their pseudorotation

The synthesis of optically active sulfinic acid esters has been accomplished by the acid catalyzed alcoholysis of optically active sulfinamides. Sulfinates are formed in this reaction with a full or predominant inversion of configuration at chiral sulfur or with predominant retention of configuration. The steric course of the reaction depends mainly on the size of the dialkylamido group in the sulfinamides and of the alcohols used as nucleophilic reagents. It has been found that bulky reaction components preferentially form sulfinates with retention of configuration. It has been demonstrated that the stereochemical outcome of the reaction can be changed from inversion to retention and vice versa by adding inorganic salts to the acidic reaction medium. The unusual stereochemistry of this typical bimolecular nucleophilic substitution reaction, as confirmed by kinetic measurements, has been rationalized in terms of the addition-elimination mechanism, A-E, involving sulfuranes as intermediates which undergo pseudorotations.

Practical and highly stereoselective method for the preparation of several chiral arylsulfinamides and arylsulfinates based on the spontaneous crystallization of diastereomerically pure N-benzyl-N-(1-phenylethyl)- arylsulfinamides

A novel and simple process for the preparation of enantiomerically pure (SS)-benzenesulfinamide (SS)-3a, (SS)-p- toluenesulfinamide (SS)-3b, (SS)-p-chloro- benzenesulfinamide (SS)-3c and (SS)-p- fluorobenzenesulfinamide (SS)-3d has been developed. The treatment of arylsulfinyl chlorides with (R)-N-benzyl-1-phenylethanamine in the presence of excess triethylamine gave diastereomeric mixtures of N-benzyl-N-(1-phenylethyl)- arylsulfinamides 1, which underwent spontaneous crystallization to furnish diastereomerically pure (R,SS)-N-benzyl-N-(1-phenylethyl)- arylsulfinamides (R,SS)-1a-1d in 28%, 29%, 27% and 31% yields, respectively. The diastereomerically pure compounds (R,SS)-1 were then converted into four enantiopure (RS)-methyl arylsulfinates (RS)-2, and finally into four enantiopure (SS)- arylsulfinamides (SS)-3 in good yields.

Chiral sulfinates studied by optical rotation, ECD and VCD: The absolute configuration of a cruciferous phytoalexin brassicanal C

The optical rotation, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) of chiral sulfinates have been studied experimentally, and analysed by density functional theory calculation, aiming at establishing a reliable and convenie

Optical Resolution of Methyl Phenyl and Benzyl Methyl Sulfoxides and Alkyl Phenylsulfinates by Complexation with Chiral Host Compounds Derived from Tartaric Acid

The title sulfoxides and sulfinates are resolved by complexation with chiral host compounds derived from tartaric acid.

NUCLEOPHILIC SUBSTITUTION AT SULFINYL AND SULFONYL CENTRES: STEREOCHEMICAL AND KINETIC STUDIES

The mechanism and stereochemistry of nucleophilic substitution reactions at sulfur (SN-S) are discussed in the light of experimental results obtained in the author's laboratory.The first part of this short review article is devoted to the acid-catalyzed alcoholysis of chiral sulfinates and sulfinamides.In the second part, the results of kinetic studies of the isotopic chloride-chloride exchange reaction in sulfonyl chlorides are presented.

Asymmetric Induction in the Reduction of Optically Active N-Alkylidenesulphinamides by Metal Hydrides. A New, Efficient Enantioselective Route to Chiral Amines

A series of racemic and optically active N-alkylidenesulphinamides has been prepared and their reduction by metal hydrides studied.The extent of asymmetric synthesis mainly depends on the nature of the reducing species; the best results (up to 92percent of stereoselectivity) are obtained with alkoxy-lithium aluminium hydrides.A new, highly enantioselective synthesis of amines is described.